alpha-Ketoisocaproic acid

Identification

Summary

alpha-Ketoisocaproic acid is an amino acid used to manage chronic renal failure and for nutritional therapy in acute renal dysfunction.

Generic Name
alpha-Ketoisocaproic acid
DrugBank Accession Number
DB03229
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 130.1418
Monoisotopic: 130.062994186
Chemical Formula
C6H10O3
Synonyms
  • 2-oxo-4-methylpentanoic acid
  • 2-Oxoisocaproate
  • 2-oxoleucine
  • 4-Methyl-2-oxopentanoate
  • 4-methyl-2-oxopentanoic acid
  • 4-methyl-2-oxovaleric acid
  • alpha-Ketoisocaproate
  • Ketoleucine
  • α-ketoisocaproic acid

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageChronic renal failure (crf)Combination Product in combination with: alpha-Ketoisocaproic acid (DB03229), Threonine (DB00156), Desmeninol (DB15832), Tyrosine (DB00135), Lysine (DB00123), Histidine (DB00117), alpha-Keto-isoleucine (DB15833), alpha-Ketoisovalerate (DB04074), Phenylpyruvic acid (DB03884)••••••••••••••••••• •••••••••••••••••
Used in combination for therapyAcute renal dysfunctionCombination Product in combination with: Histidine (DB00117), alpha-Keto-isoleucine (DB15833), Tyrosine (DB00135), alpha-Ketoisovalerate (DB04074), Threonine (DB00156), alpha-Ketoisocaproic acid (DB03229), Phenylpyruvic acid (DB03884), Desmeninol (DB15832), Lysine (DB00123)••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDeacetoxycephalosporin C synthaseNot AvailableStreptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
UD-2-hydroxyisocaproate dehydrogenaseNot AvailableLactobacillus paracasei
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
3-Hydroxy-3-methylglutaryl-CoA Lyase DeficiencyDisease
Methylmalonic AciduriaDisease
Isobutyryl-CoA Dehydrogenase DeficiencyDisease
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
beta-Ketothiolase DeficiencyDisease
Isovaleric AcidemiaDisease
Valine, Leucine, and Isoleucine DegradationMetabolic
3-Methylglutaconic Aciduria Type IIIDisease
3-Methylglutaconic Aciduria Type IVDisease
Maple Syrup Urine DiseaseDisease
Propionic AcidemiaDisease
3-Methylcrotonyl-CoA Carboxylase Deficiency Type IDisease
Isovaleric AciduriaDisease
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDisease
3-Hydroxyisobutyric Acid Dehydrogenase DeficiencyDisease
3-Hydroxyisobutyric AciduriaDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Calcium 4-methyl-2-oxovalerate5L325UH89S51828-95-6WQZNGJIBHXYVNW-UHFFFAOYSA-L

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Keto acids and derivatives
Sub Class
Short-chain keto acids and derivatives
Direct Parent
Short-chain keto acids and derivatives
Alternative Parents
Methyl-branched fatty acids / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Alpha-hydroxy ketone / Alpha-keto acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acyl / Hydrocarbon derivative / Ketone
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2-oxo monocarboxylic acid (CHEBI:48430)
Affected organisms
Not Available

Chemical Identifiers

UNII
4GUJ8AH400
CAS number
816-66-0
InChI Key
BKAJNAXTPSGJCU-UHFFFAOYSA-N
InChI
InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
IUPAC Name
4-methyl-2-oxopentanoic acid
SMILES
CC(C)CC(=O)C(O)=O

References

General References
  1. Martin PM, Gopal E, Ananth S, Zhuang L, Itagaki S, Prasad BM, Smith SB, Prasad PD, Ganapathy V: Identity of SMCT1 (SLC5A8) as a neuron-specific Na+-coupled transporter for active uptake of L-lactate and ketone bodies in the brain. J Neurochem. 2006 Jul;98(1):279-88. [Article]
Human Metabolome Database
HMDB0000695
KEGG Compound
C00233
PubChem Compound
70
PubChem Substance
46506016
ChemSpider
69
BindingDB
50390988
ChEBI
48430
ChEMBL
CHEMBL445647
ZINC
ZINC000001532578
PDBe Ligand
COI
Wikipedia
Alpha-Ketoisocaproic_acid
PDB Entries
1dxy / 1hjf / 1qs0 / 1umd / 2hdk / 2xjh / 2xji / 3uzb / 3wgy / 4h7q
show 4 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.76 mg/mLALOGPS
logP0.82ALOGPS
logP1.5Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.53Chemaxon
pKa (Strongest Basic)-9.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.37 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity31.77 m3·mol-1Chemaxon
Polarizability13 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.981
Blood Brain Barrier+0.9523
Caco-2 permeable-0.5504
P-glycoprotein substrateNon-substrate0.7659
P-glycoprotein inhibitor INon-inhibitor0.8665
P-glycoprotein inhibitor IINon-inhibitor0.923
Renal organic cation transporterNon-inhibitor0.9552
CYP450 2C9 substrateNon-substrate0.8451
CYP450 2D6 substrateNon-substrate0.9087
CYP450 3A4 substrateNon-substrate0.6812
CYP450 1A2 substrateNon-inhibitor0.9506
CYP450 2C9 inhibitorNon-inhibitor0.9094
CYP450 2D6 inhibitorNon-inhibitor0.9578
CYP450 2C19 inhibitorNon-inhibitor0.9616
CYP450 3A4 inhibitorNon-inhibitor0.9712
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9892
Ames testNon AMES toxic0.9491
CarcinogenicityNon-carcinogens0.5126
BiodegradationReady biodegradable0.9073
Rat acute toxicity1.5348 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9909
hERG inhibition (predictor II)Non-inhibitor0.9673
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-000i-9400000000-49d055f04bfe1877ac5b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-029j-8930000000-c6c54bf6ee2995a2195b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-1910000000-0ba38257e25873312809
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0a5c-4930000000-61247369a805fa2a77a7
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000i-9510000000-8bfc5a54e29f65edf361
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-00lj-9620000000-aa8409ceb2359d903f38
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9000000000-e410bce23706f826f8dd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-9400000000-49d055f04bfe1877ac5b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-029j-8930000000-c6c54bf6ee2995a2195b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1910000000-0ba38257e25873312809
GC-MS Spectrum - GC-MSGC-MSsplash10-0a5c-4930000000-61247369a805fa2a77a7
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-9510000000-8bfc5a54e29f65edf361
GC-MS Spectrum - GC-MSGC-MSsplash10-00lj-9620000000-aa8409ceb2359d903f38
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00ks-7930000000-4e9cfd715fa884d30e7f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-9500000000-709ebcb57f006703c269
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-bed7ac074a60210971e3
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-014i-9200000000-2fa08d2b4df406cf63ea
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014j-9000000000-045be8e8dca3f93d45ba
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-237fa8ad6bfb929be31e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004r-9700000000-8d38d24fce78b1ff13e6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a59-9000000000-759cfc0817917283d1a5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4l-9000000000-2a068ada71fbe0a5a988
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4l-9000000000-58e61e31f3c96d84d799
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-237fa8ad6bfb929be31e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004r-9700000000-8d38d24fce78b1ff13e6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a59-9000000000-759cfc0817917283d1a5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9000000000-2a068ada71fbe0a5a988
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9000000000-58e61e31f3c96d84d799
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0900000000-556a0d1cf568609752d1
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-004r-5900000000-20f6923c8ed45e9fa088
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052o-9000000000-78dfcbe0fe71610bd983
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-e4b0cfccf6011726e7e6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-015l-9000000000-ed2719af72e6a871f338
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-c22f0ac53b5bed44477f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9000000000-5e96dcc30b970e52c378
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-58b71ec8984e4836635d
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-128.5900066
predicted
DarkChem Lite v0.1.0
[M-H]-128.4353066
predicted
DarkChem Lite v0.1.0
[M-H]-128.3116066
predicted
DarkChem Lite v0.1.0
[M-H]-130.83794
predicted
DeepCCS 1.0 (2019)
[M+H]+129.5392066
predicted
DarkChem Lite v0.1.0
[M+H]+128.9664066
predicted
DarkChem Lite v0.1.0
[M+H]+128.8869066
predicted
DarkChem Lite v0.1.0
[M+H]+133.60197
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.4254066
predicted
DarkChem Lite v0.1.0
[M+Na]+128.4892066
predicted
DarkChem Lite v0.1.0
[M+Na]+128.3292066
predicted
DarkChem Lite v0.1.0
[M+Na]+142.23918
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Streptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
Pharmacological action
Unknown
General Function
L-ascorbic acid binding
Specific Function
Catalyzes the step from penicillin N to deacetoxy-cephalosporin C.
Gene Name
cefE
Uniprot ID
P18548
Uniprot Name
Deacetoxycephalosporin C synthase
Molecular Weight
34555.38 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Lactobacillus paracasei
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-oh group of donors, nad or nadp as acceptor
Specific Function
Catalyzes the NAD dependent reversible, stereospecific interconversion between 2-ketocarboxylic acids and D-2-hydroxy-carboxylic acids.
Gene Name
Not Available
Uniprot ID
P17584
Uniprot Name
D-2-hydroxyisocaproate dehydrogenase
Molecular Weight
36892.78 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 08, 2021 11:32